Caitlin Long (Avanti Financial Group) on Bitcoin banks and the Wyoming SPDI (EP. 101)
On The Brink with Castle Island
Release Date: 07/13/2020
Weekly Roundup 08/08/25 (Debanking EO, Storm Verdict, RMB stables) (EP.653)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: What’s wrong with NYC? China bans Bitcoin for the 15th time Is China really lauching an RMB stablecoin? We dissect the Trump debanking EO OpenAI releases GPT5 SEC: Liquid staking tokens are not securities Roman Storm is found guilty on one of three counts Hester Peirce’s speech on financial privacy How should we solve debanking? Will stablecoins replace bank wires? Is AI going to reveal the identity of Satoshi Further reading: Hester Peirce, Nic on Substack,
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Sid Powell (Maple) on Maple's Comeback & DeFi Credit Markets (EP.652)
On The Brink with Castle Island
CEO and cofounder joins the show to talk about Maple's huge year so far. In this episode: Syrup and Maple's evolution into an on-chain asset manager Traditional credit players servicing on-chain finance DeFi's strengths and weaknesses relative to traditional markets
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Weekly Roundup 08/01/25 (SEC’s Project Crypto, In-kind ETFs, White House report) (EP.651)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: The White House publishes their highly awaited crypto report SEC Chair Paul Atkins makes a landmark speech Stablecoin-focused L1s DAT mNAV premia are converging to 1 Figma IPO The SEC embraces tokenized securities, airdrops, token issuance, and DeFi In-kind create and redeem has been authorized for Bitcoin ETFs JPM deepens their partnership with Coinbase Roman Storm verdict is imminent Further reading: Blockworks’ Omid Malekan and Zach Pandl, White House, Paul Atkins, Nic Carter,
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Michael Bentley (Euler) on Euler's Comeback (EP.650)
On The Brink with Castle Island
Wyatt sits down with , the founder of . In this episode: Euler's founding story, infamous security incident, and comeback story How the team and protocol stayed together in the face of immense challenges The value of personal relationships in crypto despite a pseudonymous culture
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Weekly Roundup 07/25/25 (Tether’s GENIUS options, Defending Free Banks, Saylor’s Stretch) (EP.649)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Defending “Free Banking” from the critics – and why stablecoins are unlike free banks The American Bankers Association doesn’t like new crypto charters Tether CEO Paolo Ardoino announces the company’s plan to launch a new US-based stablecoin this year Strategy announced the plans for the fourth preferred stock offering this week, STRC, or "Stretch." Anchorage Digital, which does hold an OCC banking charter, is a new stablecoin issuance platform. The first stablecoin product will...
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Cyrus Shirazi (Haven) on Better Bookkeeping for Crypto Startups & Beyond (EP.648)
On The Brink with Castle Island
CEO of joins the show. In this episode: R&D tax credits and offering an attractive tax product to early stage companies What on-chain finance needs to fulfill becoming a better ledger for accounting What startups should look for in a tax & accounting partner
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Weekly Roundup 07/18/25 (GENIUS is Law, Clarity passes, narrow banking and GENIUS) (EP.647)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: The Coldplay concert incident It’s Crypto Week in Washington Talos acquires Coin Metrics Do you need an MTL to run a fantasy football league? GENIUS Act is law pending Trump’s signature Clarity Act passes the House ICO Fairshake raises $141m Grayscale is preparing for an IPO Adam Back’s Bitcoin access vehicle Polymarket beats the allegations Is GENIUS creating a narrow bank system? Governor Waller's comments on stablecoins and banks
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Nikhil Raghuveera (Predicate) on Policy Engines for Blockchains (EP.646)
On The Brink with Castle Island
Wyatt sits down with of to talk policy for blockchain applications. In this episode: How Predicate’s “rules for blockchain transactions” are making on-chain finance more scalable and secure Creating more compliant stablecoin transfer systems suitable to mass financial use cases The future of secure money movement How leading software and financial firms can integrate transaction policies in their workflows
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Weekly Roundup 07/11/25 (New BTC ATH, Crypto Week, Zelensky suit scandal) (EP.645)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: Bitcoin hits a new ATH and no one is talking about it Grok goes haywire The White House posts chudjak Core Weave looks to buy Core Scientific Stablecoins are going to pay yield anyway Did Zelenskyy wear a suit? How should prediction markets be settled? ICO is coming up Hester Peirce issues a warning on tokenized securities Crypto Week in Congress is coming up Jonathan Gould has been confirmed as Comptroller of the Currency There are new public access vehicles Andreessen wants you to leave Delaware A fundamental...
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Zac Townsend (Meanwhile) on Bitcoin Life Insurance (EP.644)
On The Brink with Castle Island
, the founder and CEO of , joins the show. In this episode we discuss: Zac’s background and the path that led him to start Meanwhile. The mechanics of Bitcoin denominated life insurance. How Meanwhile generates Bitcoin yield. Zac’s views on the evolution of Bitcoin treasury companies. To learn more about Meanwhile visit
info_outlineCaitlin Long, founder and CEO of Avanti Financial Group, joins the show. Caitlin is a thinker and writer we admire a huge amount and she has done a monumental job with her advocacy for responsible custody practices among crypto depository institutions. She is one of the key architects of the Wyoming Special Purpose Depository Institution legislation which establishes a new form of crypto bank in Wyoming. In in no small part thanks to her efforts that Wyoming is the most progressive state in terms of defining and regulating digital assets and the institutions that custody them. We share Caitlin's enthusiasm for clarifying depositor exchange relationships and for public-facing proofs of reserve, so we were very excited have her on the show. Covered in this episode:
- Risks involved in complying with the FATF's travel rule
- How the FATF enforces its recommendations
- Why compliance burdens freeze out small and community banks
- How the $10k limit for disclosure for cash transactions increases the scope of transactions that should be disclosed in real terms
- How the Bank Secrecy Act and the third party doctrine means the government can procure warrantless financial data
- Caitlin's Bitcoin origin story
- The thawing of the gold community's sentiments towards bitcoin
- The tension inherent in the institutionalization of bitcoin
- Why Proofs of Reserves aren't more popular today
- The importance of distinguishing ownership of a key and a legal title
- Why users are poorly equipped to hold exchanges accountable
- Why the state by state regulation in the US doesn't suit the reality of crypto custodians
- How the Wyoming SPDI legislation got started
- What the Wyoming SPDI laws actually mean
- How Avanti got its name
- Caitlin's long term objectives with Avanti
- Why banking remains the achilles heel of the crypto industry
- Why existing banks might not be able to handle future growth of the crypto industry
- How the FDIC targeted the crypto industry
- Why custodians should have access to the Fed window
- Caitlin's pitch to entrepreneurs to move to Wyoming